2-Naphthalenol

• Formula: C₁₀H₈O
• Molecular weight: 144.1699
• IUPAC Standard InChI: InChI=1S/C10H8O/c11-10-6-5-8-3-1-2-4-9(8)7-10/h1-7,11H Copy

  
• IUPAC Standard InChIKey: JWAZRIHNYRIHIV-UHFFFAOYSA-N Copy
• CAS Registry Number: 135-19-3
• Chemical structure:
  This structure is also available as a 2d Mol file or as a computed 3d SD file
  The 3d structure may be viewed using Java or Javascript.
• Other names: β-Naphthol; 2-Naphthol; β-Hydroxynaphthalene; Azogen Developer A; Betanaphthol; C.I. Azoic Coupling Component 1; C.I. Developer 5; C.I. 37500; Developer A; Developer AMS; Developer BN; Isonaphthol; Naphthol B; 2-Hydroxynaphthalene; β-Monoxynaphthalene; β-Naftol; β-Naftolo; β-Naphthyl alcohol; β-Naphthyl hydroxide; β-Naphtol; β-Napthol; Naphthol, β; 2-Naftol; 2-Naftolo; 2-Naphtol; Antioxygene BN; NSC 2044
• Permanent link for this species. Use this link for bookmarking this species for future reference.
• Information on this page:
  • Gas phase thermochemistry data
  • Condensed phase thermochemistry data
  • Phase change data
  • Reaction thermochemistry data
  • Gas phase ion energetics data
  • IR Spectrum
  • Mass spectrum (electron ionization)
  • Gas Chromatography
  • References
  • Notes
• Other data available:
  • UV/Visible spectrum
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Gas phase thermochemistry data

Go To: Top, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DRB - Donald R. Burgess, Jr.
GT - Glushko Thermocenter, Russian Academy of Sciences, Moscow

Constant pressure heat capacity of gas

Condensed phase thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Constant pressure heat capacity of solid

Phase change data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled as indicated in comments:
BS - Robert L. Brown and Stephen E. Stein
TRC - Thermodynamics Research Center, NIST Boulder Laboratories, Chris Muzny director
AC - William E. Acree, Jr., James S. Chickos
DRB - Donald R. Burgess, Jr.
ALS - Hussein Y. Afeefy, Joel F. Liebman, and Stephen E. Stein
DH - Eugene S. Domalski and Elizabeth D. Hearing

Enthalpy of vaporization

Antoine Equation Parameters

log₁₀(P) = A − (B / (T + C))
    P = vapor pressure (bar)
    T = temperature (K)

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Enthalpy of sublimation

Enthalpy of fusion

Entropy of fusion

Reaction thermochemistry data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: John E. Bartmess

Note: Please consider using the reaction search for this species. This page allows searching of all reactions involving this species. A general reaction search form is also available. Future versions of this site may rely on reaction search pages in place of the enumerated reaction displays seen below.

Individual Reactions

C₁₀H₇O^- +  =

By formula: C₁₀H₇O^- + H⁺ = C₁₀H₈O

Gas phase ion energetics data

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data evaluated as indicated in comments:
L - Sharon G. Lias

Data compiled as indicated in comments:
B - John E. Bartmess
LBLHLM - Sharon G. Lias, John E. Bartmess, Joel F. Liebman, John L. Holmes, Rhoda D. Levin, and W. Gary Mallard
LLK - Sharon G. Lias, Rhoda D. Levin, and Sherif A. Kafafi
RDSH - Henry M. Rosenstock, Keith Draxl, Bruce W. Steiner, and John T. Herron

Ionization energy determinations

Appearance energy determinations

De-protonation reactions

C₁₀H₇O^- +  =

By formula: C₁₀H₇O^- + H⁺ = C₁₀H₈O

IR Spectrum

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Data compiled by: Coblentz Society, Inc.

• Not specified, most likely a prism, grating, or hybrid spectrometer.; (NO SPECTRUM, ONLY SCANNED IMAGE IS AVAILABLE)

Data compiled by: Timothy J. Johnson, Tanya L. Myers, Yin-Fong Su, Russell G. Tonkyn, Molly Rose K. Kelly-Gorham, and Tyler O. Danby

• solid; Bruker IR Cube FTIR; 0.96450084 cm^-1 resolution

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

• gas

Mass spectrum (electron ionization)

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Spectrum

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Additional Data

Gas Chromatography

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Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Data compiled by: NIST Mass Spectrometry Data Center, William E. Wallace, director

Kovats' RI, non-polar column, isothermal

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Van Den Dool and Kratz RI, non-polar column, temperature ramp

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Van Den Dool and Kratz RI, non-polar column, custom temperature program

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Normal alkane RI, non-polar column, temperature ramp

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Normal alkane RI, non-polar column, custom temperature program

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Lee's RI, non-polar column, temperature ramp

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References

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, Notes

Data compilation copyright by the U.S. Secretary of Commerce on behalf of the U.S.A. All rights reserved.

Ribeiro Da Silva, Ribeiro Da Silva, et al., 1988
Ribeiro Da Silva, M.A.V.; Ribeiro Da Silva, M.D.M.C.; Pilcher, G., Enthalpies of combustion of 1-hydroxynaphthalene, 2-hydroxynaphthalene, and 1,2-, 1,3-, 1,4-, and 2,3-dihydroxynaphthalenes, J. Chem. Thermodyn., 1988, 20, 969-974. [all data]

Colomina, Roux, et al., 1974
Colomina, M.; Roux, M.V.; Turrion, C., Thermochemical properties of naphthalene compounds. I. Enthalpies of combustion and formation of the 1- and 2-naphthoic acids, J. Chem. Thermodyn., 1974, 6, 149-155. [all data]

Colomina, Roux, et al., 1974, 2
Colomina, M.; Roux, M.V.; Turrion, C., Thermochemical properties of naphthalene compounds. II. Enthalpies of combustion and formation of the 1- and 2-naphthols, J. Chem. Thermodyn., 1974, 6, 571-576. [all data]

Pushin, 1954
Pushin, N.A., Heats of combustion and heats of formation of isomeric organic compounds, Bull. Soc. Chim. Belgrade, 1954, 19, 531-547. [all data]

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Danilenko, Danilenko, et al., 1974
Danilenko, V.E.; Danilenko, G.N.; Demidenko, A.F., Thermodynamic properties of β-naphthol and 2,3-dihydroxynaphthalene, Zhur. Fiz. Khim., 1974, 48, 1886. [all data]

Andrews, Lynn, et al., 1926
Andrews, D.H.; Lynn, G.; Johnston, J., The heat capacities and heat of crystallization of some isomeric aromatic compounds, J. Am. Chem. Soc., 1926, 48, 1274-1287. [all data]

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Mantyukov, Loginova, et al., 1974
Mantyukov, G.D.; Loginova, M.A.; Bychkov, B.N.; Rozhkov, S.S., Liquid-vapor equilibrium in the system isopropylnaphthalene + 2-naphthol, J. Appl. Chem. USSR (Engl. Transl.), 1974, 47, 2665-6. [all data]

May, Berliner, et al., 1927
May, O.E.; Berliner, J.F.T.; Lynch, D.F.J., Studies in Vapor Pressure IV. The Naphthols, J. Am. Chem. Soc., 1927, 49, 1012. [all data]

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Chickos, James S.; Hosseini, Sarah; Hesse, Donald G., Determination of vaporization enthalpies of simple organic molecules by correlations of changes in gas chromatographic net retention times, Thermochimica Acta, 1995, 249, 41-62, https://doi.org/10.1016/0040-6031(95)90670-3 . [all data]

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von Terres, Gebert, et al., 1955
von Terres, E.; Gebert, F.; Hulsemann, H.; Petereit, H.; Toepsch, H.; Ruppert, W., Brennst.-Chem., 1955, 36, 272. [all data]

May, Berliner, et al., 1927, 2
May, Orville E.; Berliner, J.F.T.; Lynch, D.F.J., STUDIES IN VAPOR PRESSURE. IV. THE NAPHTHOLS, J. Am. Chem. Soc., 1927, 49, 4, 1012-1016, https://doi.org/10.1021/ja01403a018 . [all data]

von Terres, Gebert, et al., 1955, 2
von Terres, E.; Gebert, F.; Hulsemann, H.; Petereit, H.; Toepsch, H.; Ruppert, W., Zur Kenntnis der physikalisch-chemischen Grundlagen der Gewinnung und Zerlegung der Phenolfraktionen von Steinkohlenteer und Braunkohlenschwelteer. IV. Mitteilung Die Dampfdrucke von Phenol und Phenolderivaten, Brennst.-Chem., 1955, 36, 272-274. [all data]

Aihara, 1960
Aihara, Ariyuki, Estimation of the Energy of Hydrogen Bonds Formed in Crystals. II. Phenols, Bull. Chem. Soc. Jpn., 1960, 33, 2, 194-200, https://doi.org/10.1246/bcsj.33.194 . [all data]

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Arshadi, Mohammed R., Determination of heats of sublimation of organic compounds by a mass spectrometric--knudsen effusion method, J. Chem. Soc., Faraday Trans. 1, 1974, 70, 0, 1569, https://doi.org/10.1039/f19747001569 . [all data]

Karyakin, Rabinovich, et al., 1968
Karyakin, N.V.; Rabinovich, I.B.; Pakhomov, L.G., Heats of sublimation of naphthalene and its monosubstituted β-derivatives, Russ. J. Phys. Chem. (Engl. Transl.), 1968, 42, 954. [all data]

May, Berliner, et al., 1927, 3
May, O.E.; Berliner, J.F.T.; Lynch, D.F.J., Studies in vapor pressure. IV. The naphthols, J. Am. Chem. Soc., 1927, 49, 1012-10. [all data]

Rojas and Orozco, 2003
Rojas, Aarón; Orozco, Eulogio, Measurement of the enthalpies of vaporization and sublimation of solids aromatic hydrocarbons by differential scanning calorimetry, Thermochimica Acta, 2003, 405, 1, 93-107, https://doi.org/10.1016/S0040-6031(03)00139-4 . [all data]

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Acree, William E., Thermodynamic properties of organic compounds: enthalpy of fusion and melting point temperature compilation, Thermochimica Acta, 1991, 189, 1, 37-56, https://doi.org/10.1016/0040-6031(91)87098-H . [all data]

Taft, 1987
Taft, R.W., The Nature and Analysis of Substitutent Electronic Effects, Personal communication. See also Prog. Phys. Org. Chem., 1987, 16, 1. [all data]

Oikawa, Abe, et al., 1985
Oikawa, A.; Abe, H.; Mikami, N.; Ito, M., Electronic spectra and ionization potentials of rotational isomers of severaldDisubstituted benzenes, Chem. Phys. Lett., 1985, 116, 50. [all data]

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Potapov, V.K.; Kardash, I.E.; Sorokin, V.V.; Sokolov, S.A.; Evlasheva, T.I., Photoionization of heteroaromatic compounds, Khim. Vys. Energ., 1972, 6, 392. [all data]

Utsunomiya, Kobayashi, et al., 1975
Utsunomiya, C.; Kobayashi, T.; Nagakura, S., Photoelectron spectra of substituted naphthalenes, Bull. Chem. Soc. Jpn., 1975, 48, 1852. [all data]

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Notes

Go To: Top, Gas phase thermochemistry data, Condensed phase thermochemistry data, Phase change data, Reaction thermochemistry data, Gas phase ion energetics data, IR Spectrum, Mass spectrum (electron ionization), Gas Chromatography, References

• Symbols used in this document:
  

  AE	Appearance energy
  Cp,gas	Constant pressure heat capacity of gas
  Cp,solid	Constant pressure heat capacity of solid
  IE (evaluated)	Recommended ionization energy
  S°gas	Entropy of gas at standard conditions
  S°solid,1 bar	Entropy of solid at standard conditions (1 bar)
  Tboil	Boiling point
  Tfus	Fusion (melting) point
  Ttriple	Triple point temperature
  ΔcH°solid	Enthalpy of combustion of solid at standard conditions
  ΔfH°gas	Enthalpy of formation of gas at standard conditions
  ΔfH°solid	Enthalpy of formation of solid at standard conditions
  ΔfusH	Enthalpy of fusion
  ΔfusS	Entropy of fusion
  ΔrG°	Free energy of reaction at standard conditions
  ΔrH°	Enthalpy of reaction at standard conditions
  ΔsubH	Enthalpy of sublimation
  ΔsubH°	Enthalpy of sublimation at standard conditions
  ΔvapH	Enthalpy of vaporization
  ΔvapH°	Enthalpy of vaporization at standard conditions

• Data from NIST Standard Reference Database 69: NIST Chemistry WebBook
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